The air is crisp, the leaves are turning brilliant shades of gold and red, and pumpkin spice is everywhere. Fall in Boston is truly a magical time. For older adults, families, and anyone who loves New England charm, this season offers endless opportunities to soak in the scenery, explore the outdoors, and enjoy seasonal traditions.
If you’re ready to celebrate autumn in style, we’ve gathered a list of the best fall foliage drives in and around Boston, plus bonus ideas for seasonal activities, day trips, and cozy stops along the way.
Drive Around Boston Common – Then Have a Picnic
There are plenty of beautiful fall colors to see throughout Boston Common. Take a drive around the perimeter or park and go for a walk. If you decide to take off by foot, consider exploring the public garden.
Take the Scenic Route Along the Charles River
Take Memorial Drive in Cambridge to see the foliage of Boston over the Charles River. If you prefer to ride your bike, ride along the Charles River Esplanade.
Want to see the foliage from a different perspective? Try a fall foliage sightseeing cruise.
Drive (or Walk!) Around Arnold Arboretum
Harvard’s Arnold Arboretum is a great place to leaf peep! Explore the 281-acre landscape by foot or drive along the roads to enjoy a brief look of all the colors.
Travel Along Freedom Trail®
Take in a little history during this gorgeous season by stopping along historical sites on the Freedom Trail®. As you travel to each stop, you’ll see stunning views while enjoying the opportunity to learn.
Go Beyond Boston
If you’re up for a longer drive, Boston is perfectly located for easy day trips to some of New England’s most scenic foliage routes:
Kancamagus Highway (NH): A world-famous drive through the White Mountain National Forest, perfect for peak foliage season.
Mohawk Trail (Western MA): Known as one of the first scenic byways in the U.S., this route offers mountain views and quaint towns.
Walden Pond (Concord, MA): Famous for its literary ties to Henry David Thoreau, the pond is especially peaceful in autumn.
Jacob’s Ladder Scenic Byway (Berkshires): A winding road with classic small-town stops and expansive views.
Seasonal Activities to Add to Your Drive
Why stop at a scenic view when you can make a whole day of it? Here are some classic New England autumn activities to pair with your foliage drive:
Fall Festivals & Craft Fairs: Check community calendars for local harvest events, hayrides, or live music
Apple Picking & Cider Tasting: Visit nearby orchards for apple picking, cider donuts, and fresh-pressed cider.
Pumpkin Patches & Farmstands: Take home seasonal produce or carve a pumpkin with the grandkids.
Local Cafés & Bakeries: Warm up with pumpkin spice lattes, mulled cider, or classic New England clam chowder.
Autumn at Waterstone at the Circle
You don’t even need to leave home to enjoy fall foliage when you live at Waterstone at the Circle. Our community offers:
- Stunning autumn views from the fifth-floor lounge balcony.
- Easy walks to Cassidy Park and Chestnut Hill Reservoir.
- Cozy gathering spaces to relax with a warm drink after a day out.
Here, residents enjoy the best of both worlds: easy access to Boston’s culture and history alongside the comfort of a supportive, luxury retirement community.
Final Thoughts
There’s nothing like autumn in New England, and Boston is one of the best places to experience it. Whether you’re setting out for a scenic drive, exploring historic landmarks, or simply enjoying the colors from your own window, fall is the perfect season to savor life’s beauty.
At Waterstone at the Circle, residents are surrounded by both the vibrancy of Boston and the comfort of community living. Contact us today to schedule a tour and see for yourself why this is home.